CN108003894B - Liquid crystal compound, liquid crystal composition and liquid crystal display device using the same - Google Patents

Liquid crystal compound, liquid crystal composition and liquid crystal display device using the same Download PDF

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CN108003894B
CN108003894B CN201710874013.5A CN201710874013A CN108003894B CN 108003894 B CN108003894 B CN 108003894B CN 201710874013 A CN201710874013 A CN 201710874013A CN 108003894 B CN108003894 B CN 108003894B
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CN108003894A (en
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吴忠宪
李清田
王俊智
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Daxin Materials Corp
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    • C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
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    • C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
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Abstract

The invention provides a liquid crystal compound, a liquid crystal composition and a liquid crystal display device using the liquid crystal compound. The liquid crystal compound has a structure represented by formula (I):

Description

Liquid crystal compound, liquid crystal composition and liquid crystal display device using the same
Technical Field
The present invention relates to a liquid crystal compound, a liquid crystal composition and a liquid crystal display device using the liquid crystal compound.
Background
Liquid crystal displays are currently used in personal computers, Personal Digital Assistants (PDAs), mobile phones, televisions, etc. because of their advantages of being light, low power consumption, and non-radiative.
Has a high vertical dielectric constant for the liquid crystal material in the liquid crystal display⊥) Liquid-crystalline compounds having low viscosity are in accordance with the present demand. In particular, when the liquid crystal material has a high vertical dielectric constant, it is possible to make a FFS (fringe field switching) liquid crystal display device of the boundary electric field switching type have a high light transmittance.
Liquid crystal compounds having both high vertical dielectric constant and UV stability are sought in the art.
Disclosure of Invention
One embodiment of the present invention discloses a liquid crystal compound having a structure represented by formula (I):
Figure BDA0001417912590000011
wherein when n1 is 0, n2 is 0, and X1 is
Figure BDA0001417912590000012
X2 is-O-and X3 is-CH2-R1, R2 may each independently of one another be H, C1-C15Alkyl radical, C2-C15Alkenyl or C2-C15Alkynyl, and wherein C1-C15Alkyl radical, C2-C15Alkenyl or C2-C15Alkynyl is unsubstituted or at least one-CH2-by-CF2O-, -CO-O-or-O-CO-and/or at least one hydrogen atom is replaced by a halogen atom; (ii) a Or
When n1 ═ 0, n2 ═ 0 and X1 are
Figure BDA0001417912590000013
When X2 is ═ CH-, and X3 is a single bond, R1 and R2 may each be, independently of one another, H, C1-C15Alkyl radical, C2-C15Alkenyl or C2-C15Alkynyl, and wherein C1-C15Alkyl radical, C2-C15Alkenyl or C2-C15Alkynyl is unsubstituted or at least one-CH2-by-CF2O-, -CO-O-or-O-CO-and/or at least one hydrogen atom is replaced by a halogen atom; or
When n1 is 1, n2 is 1 or 0, X1 is
Figure BDA0001417912590000021
When X2 is ═ CH —, and X3 is a single bond, R1 and R2 may each independently be H, a halogen atom, or C1-C15Alkyl radical, C2-C15Alkenyl or C2-C15Alkynyl, and wherein C1-C15Alkyl radical, C2-C15Alkenyl or C2-C15Alkynyl is unsubstituted or at least one-CH2-by-CF2O-, -CO-O-or-O-CO-and/or at least one hydrogen atom is replaced by a halogen atom, and the cyclic group A is 1, 4-phenylene or 1, 4-cyclohexylene.
Another embodiment of the present invention discloses a liquid crystal composition comprising a first component and a second component, wherein the first component comprises one or more liquid crystal compounds represented by the above formula (I), and the second component comprises one or more compounds represented by the following formula (II):
Figure BDA0001417912590000022
wherein R3 and R4 are each independently H, halogen atom, C1-C15Alkyl or C2-C15Alkenyl radical, and wherein C1-C15Alkyl or C2-C15Alkenyl is unsubstituted or at least one hydrogen atom is substituted by a halogen atom, and/or at least one-CH2-is substituted by-O-and-O-is not directly linked to-O-;
a1, A2, A3 are each independently 1, 4-phenylene, 1, 4-cyclohexylene, 2, 5-benzofuranylene or 2, 5-tetrahydropyranyl, wherein 1, 4-phenylene, 1, 4-cyclohexylene, 2, 5-benzofuranylene or 2, 5-tetrahydropyranyl is unsubstituted or at least one hydrogen atom is substituted by a F atom;
z1 and Z2 are each independently a single bond, C1-C4Alkylene radical, C2-C4Alkenylene radical, C2-C4Alkynylene, and wherein C1-C4Alkylene radical, C2-C4Alkenylene or C2-C4Alkynylene is unsubstituted or substituted by CN on at least one hydrogen atom, and/or by at least one-CH2-is substituted by-O-or-S-, and-O-is not directly linked to-O-or-S-and-S-is not directly linked to-S-; and
u is 0, 1 or 2.
Another embodiment of the present invention discloses a liquid crystal display device, including: a first substrate; a second substrate disposed opposite to the first substrate; and a liquid crystal layer between the first substrate and the second substrate, wherein the liquid crystal layer comprises a liquid crystal compound represented by the formula (I).
In order to make the aforementioned and other objects, features, and advantages of the present invention comprehensible, preferred embodiments accompanied with figures are described in detail below:
drawings
FIG. 1 is a schematic cross-sectional view illustrating an LCD device according to some embodiments of the present invention.
Detailed Description
The invention provides aLiquid crystal compounds, which in some embodiments may have a high vertical dielectric constant(s) ((s))⊥>10) And simultaneously has good UV stability. More specifically, the liquid crystal compound of the present invention has a dielectric anisotropy (Δ) that varies by ± 5% after being irradiated with UV light for 90 minutes. In other words, the dielectric anisotropy Δ' after the irradiation of the UV light for 90 minutes is in the range of 95% to 105% of the dielectric anisotropy Δ before the irradiation of the UV light.
In some embodiments, the present disclosure provides a liquid crystal compound having a structure represented by the following formula (I):
Figure BDA0001417912590000031
wherein when n1 is 0, n2 is 0, and X1 is
Figure BDA0001417912590000032
X2 is-O-and X3 is-CH2-
When R1, R2 may each be, independently of one another, H, C1-C15Alkyl radical, C2-C115Alkenyl or C2-C15Alkynyl, and wherein C1-C15Alkyl radical, C2-C15Alkenyl or C2-C15Alkynyl is unsubstituted or at least one-CH2-by-CF2O-, -CO-O-or-O-CO-and/or at least one hydrogen atom is replaced by a halogen atom; or
When n1 ═ 0, n2 ═ 0 and X1 are
Figure BDA0001417912590000033
When X2 is ═ CH-, and X3 is a single bond, R1 and R2 may each be, independently of one another, H, C1-C15Alkyl radical, C2-C15Alkenyl or C2-C15Alkynyl, and wherein C1-C15Alkyl radical, C2-C15Alkenyl or C2-C15Alkynyl is unsubstituted or at least one-CH2-by-CF2O-, -CO-O-or-O-CO-substituted, and/or at least one hydrogen atom is replaced byHalogen atom substitution; or
When n1 is 1, n2 is 1 or 0, X1 is
Figure BDA0001417912590000034
When X2 is ═ CH —, and X3 is a single bond, R1 and R2 may each independently be H, a halogen atom, or C1-C15Alkyl radical, C2-C15Alkenyl or C2-C15Alkynyl, and wherein C1-C15Alkyl radical, C2-C15Alkenyl or C2-C15Alkynyl is unsubstituted or at least one-CH2-by-CF2O-, -CO-O-or-O-CO-and/or at least one hydrogen atom is replaced by a halogen atom, and the cyclic group A is 1, 4-phenylene or 1, 4-cyclohexylene.
Since the following description uses various liquid crystal compounds, for the sake of simplicity of representation, the following will be represented by combinations of symbols in which O represents an oxygen atom; f represents a fluorine atom; and the structural units corresponding to each code are shown in the following table 1.
TABLE 1
Figure BDA0001417912590000041
It should be noted that in the structural units shown in Table 1, X represents the bonding position of the bonding group at the left end of the structural unit, and Y represents the bonding position of the bonding group at the right end of the structural unit. In other words, when only X is contained in the structural formula, it represents that the structural unit is the rightmost structural unit of the liquid crystal compound. Further, the number shown in a non-subscript letter represents an alkyl group having a carbon number equal to the number. For example, the code 3CCV represents an alkyl group (i.e., a propyl group) of 3 carbons, a structural unit C and a structural unit V in this order from left to right of the compound. In other words, 3CCV represents a compound having the structure:
Figure BDA0001417912590000051
in addition, the combination of the above codes is directly combined according to the structural positions and directions shown in Table 1, for example, 3PGQIof tableA compound having the structure:
Figure BDA0001417912590000052
rather than that of
Figure BDA0001417912590000053
The structure shown in formula (I) is a rod-shaped structure. Such a rod-like structure has a first axial direction and a second axial direction. The first axial direction is a long axis direction of the rod-like structure, i.e., a direction connecting the functional group R1 and the functional group R2. The second axial direction is a short axial direction of the rod-like structure, i.e., a direction perpendicular to the first axial direction. In the above formula (I), the hydrogen atoms on two adjacent carbon atoms on the benzene ring are substituted by fluorine atoms. Since fluorine is a substituent having a very strong electron withdrawing ability, the liquid crystal compound represented by formula (I) can have a very large polarity in the short axis direction. Therefore, the liquid crystal compound represented by the formula (I) has a high vertical dielectric anisotropy: (⊥). In the formula (I), the carbon atoms adjacent to the two carbon atoms having the fluorine substituent are bonded to one oxygen atom. Since the oxygen atom has two unshared lone pairs of electrons, it can be used as an electron source to provide electrons to the benzene ring. Therefore, the vertical dielectric constant of the liquid crystal compound represented by the formula (I) can be further improved.
As described above, the liquid crystal compound having the structure of formula (I) according to the present invention has a high vertical dielectric constant due to the electron withdrawing property of fluorine atoms and the electron donating property of oxygen atoms. In some embodiments, liquid crystal compounds having the structure of formula (I)⊥>10. In other embodiments, the liquid crystal compounds having the structure of formula (I)⊥>12. In still other embodiments, the liquid crystal compounds having the structure of formula (I)⊥>14。
According to some embodiments of the present invention, in formula (I), n1 ═ 0, n2 ═ 0, and X1 are
Figure BDA0001417912590000054
X2 is-O-and X3 is-CH2-. In such an embodimentThe liquid crystal compound may have a structure represented by formula (I-A):
Figure BDA0001417912590000055
in the formula (I-A), R1, R2 may each be, independently of one another, H, C1-C15Alkyl radical, C2-C15Alkenyl or C2-C15Alkynyl, and wherein C1-C15Alkyl radical, C2-C15Alkenyl or C2-C15Alkynyl is unsubstituted or at least one-CH2-by-CF2O-, -CO-O-or-O-CO-and/or at least one hydrogen atom is replaced by a halogen atom.
Referring to formula (I-A) and Table 1, formula (I-A) includes structural element OSy. Structural unit OSy includes a specific benzene ring structure as described above (i.e., 4 carbon atoms on the benzene ring are bonded to an oxygen atom, a fluorine atom, and an oxygen atom in that order). As described above, since a specific carbon atom of the benzene ring has a fluorine atom and an oxygen atom, the liquid crystal compound having the structure represented by formula (I-A) can have a high vertical dielectric constant. In addition, the liquid crystal compound having the structure represented by formula (I-a) may have excellent UV stability. In some embodiments, the liquid crystal compound having the structure represented by formula (I-a) has a dielectric anisotropy (Δ) that varies by ± 5% after being irradiated with UV light for 90 minutes. In other embodiments, the liquid crystal compound having the structure represented by formula (I-A) has a dielectric anisotropy (Δ) that varies by ± 2% after being irradiated with UV light for 90 minutes.
The liquid crystal compound having the structure represented by the formula (I-A) can be adjusted in properties such as viscosity, resistance, intermolecular force, etc. by changing the functional groups R1 and R2. Further, since it is difficult to synthesize, the liquid crystal compound having the structure represented by formula (I-a) does not include a cyclic group (for example, an aromatic ring or an aliphatic ring) in the functional group R1 and the functional group R2. In some embodiments, at least one of R1, R2 is unsubstituted C1-C15Alkyl or unsubstituted C2-C15An alkenyl group. In other embodiments, at least one of R1, R2 is unsubstituted C1-C6Alkyl or unsubstituted C2-C6An alkenyl group.
According to some embodiments of the present invention, in formula (I), n1 ═ 0, n2 ═ 0, and X1 are
Figure BDA0001417912590000062
X2 is ═ CH-, and X3 is a single bond. In such embodiments, one end of X2 is double bonded to X1 and the other end is single bonded to a carbon atom on the phenyl ring. In other words, in such embodiments, the liquid crystal compound may have a structure represented by formula (I-B-1):
Figure BDA0001417912590000061
in the formula (I-B-1), R1, R2 may each be, independently of one another, H, C1-C15Alkyl radical, C2-C15Alkenyl or C2-C15Alkynyl, and wherein C1-C15Alkyl radical, C2-C15Alkenyl or C2-C15Alkynyl is unsubstituted or at least one-CH2-by-CF2O-, -CO-O-or-O-CO-and/or at least one hydrogen atom is replaced by a halogen atom.
Referring to formula (I-B-1) and Table 1, formula (I-B-1) includes structural unit ByO. Structural unit ByO also includes the specific benzene ring structure described above (i.e., 4 carbon atoms on the benzene ring are bonded in order to an oxygen atom, a fluorine atom, and an oxygen atom). As described above, in the formula (I-B-1), since the specific carbon atom of the benzene ring has a fluorine atom and an oxygen atom, the liquid crystal compound having the structure represented by the formula (I-B-1) can also have a high perpendicular dielectric constant. Further, the liquid crystal compound having the structure represented by formula (I-B-1) may also have good UV stability. In some embodiments, the liquid crystal compound having the structure represented by formula (I-B-1) has a dielectric anisotropy (Δ) that varies by ± 5% after being irradiated with UV light for 90 minutes. In other embodiments, the liquid crystal compound having the structure represented by formula (I-B-1) has a dielectric anisotropy (Δ) that varies by ± 2% after being irradiated with UV light for 90 minutes.
Further, in the formula (I-B-1), the carbon atom bonded to the functional group R2 includes a double bond, and such a structure contributes to lowering the viscosity of the liquid crystal compound. On the contrary, if the carbon atom is in a saturated state (i.e. the 4 bonds of the carbon atom are all single bonds, excluding any double bonds), the liquid crystal compound with such a structure has a high viscosity, which is not suitable for application in a display device.
The liquid crystal compound having the structure represented by the formula (I-B-1) can be modified in properties such as viscosity, electric resistance, intermolecular force, etc. by changing the functional groups R1 and R2. In some embodiments, at least one of R1, R2 is unsubstituted C1-C15Alkyl or unsubstituted C2-C15An alkenyl group. In other embodiments, at least one of R1, R2 is unsubstituted C1-C10Alkyl or unsubstituted C2-C10An alkenyl group. In other embodiments, at least one of R1, R2 is unsubstituted C1-C6Alkyl or unsubstituted C2-C6An alkenyl group.
According to some embodiments of the present invention, in formula (I), n1 ═ 1, n2 ═ 1 or 0, and X1 are
Figure BDA0001417912590000072
X2 is ═ CH-, and X3 is a single bond. Similarly, in such embodiments, one end of X2 is double bonded to X1 and the other end is single bonded to a carbon atom on the phenyl ring. In other words, in such embodiments, the liquid crystal compound may have a structure represented by formula (I-B-2) or formula (I-B-3):
Figure BDA0001417912590000071
r1 and R2 may each independently be H, a halogen atom, C1-C15Alkyl radical, C2-C15Alkenyl or C2-C15Alkynyl, and wherein C1-C15Alkyl radical, C2-C15Alkenyl or C2-C15Alkynyl is unsubstituted or at least one-CH2-by-CF2O-, -CO-O-or-O-CO-and/or at least one hydrogen atom is replaced by a halogen atom, and the cyclic group A is 1, 4-phenylene or 1, 4-cyclohexylene.
Referring to formula (I-B-2), formula (I-B-3) and Table 1, structural element ByO is also included in formula (I-B-2) or formula (I-B-3). As described above, the liquid crystal compound having the structure represented by formula (I-B-2) or formula (I-B-3) may also have a high perpendicular dielectric constant.
Furthermore, both the formula (I-B-2) and the formula (I-B-3) comprise structural units G. Structural unit G contributes to improvement in UV stability of a liquid crystal compound having structural unit ByO together with other cyclic groups (e.g., aromatic rings). In other words, if the structural unit G in the liquid crystal compound represented by the formula (I-B-2) or the formula (I-B-3) is replaced with a1, 4-phenylene group, the resulting liquid crystal compound has poor UV stability. In some embodiments, the liquid crystal compound having a structure represented by formula (I-B-1), formula (I-B-2), or formula (I-B-3) has a dielectric anisotropy (Δ) that varies by ± 5% after being irradiated with UV light for 90 minutes.
Further, formula (I-B-3) includes other cyclic groups (i.e., cyclic group A) in addition to structural unit G. In some embodiments, the number n2 of cyclic groups a is 1.
The liquid crystal compound having the structure represented by the formula (I-B-2) or (I-B-3) can be modified in properties such as viscosity, electric resistance, intermolecular force, etc., by changing the functional groups R1 and R2. In some embodiments, at least one of R1, R2 is unsubstituted C1-C15Alkyl or unsubstituted C2-C15An alkenyl group. In other embodiments, at least one of R1, R2 is unsubstituted C1-C10Alkyl or unsubstituted C2-C10An alkenyl group. In other embodiments, at least one of R1, R2 is unsubstituted C1-C6Alkyl or unsubstituted C2-C6An alkenyl group.
In some embodiments, the present invention also provides a liquid crystal composition comprising a first component and a second component, wherein the first component comprises one or more liquid crystal compounds represented by formula (I) above, and the second component comprises one or more compounds represented by formula (II) below:
Figure BDA0001417912590000081
wherein R3 and R4 are each independently H, halogen atom, C1-C15Alkyl or C2-C15Alkenyl radical, and wherein C1-C15Alkyl or C2-C15Alkenyl is unsubstituted or at least one hydrogen atom is substituted by a halogen atom, and/or at least one-CH2-is substituted by-O-and-O-is not directly linked to-O-;
a1, A2, A3 are each independently 1, 4-phenylene, 1, 4-cyclohexylene, 2, 5-benzofuranylene or 2, 5-tetrahydropyranyl, wherein 1, 4-phenylene, 1, 4-cyclohexylene, 2, 5-benzofuranylene or 2, 5-tetrahydropyranyl is unsubstituted or at least one hydrogen atom is substituted by a F atom;
z1 and Z2 are each independently a single bond, C1-C4Alkylene radical, C2-C4Alkenylene radical, C2-C4Alkynylene, and wherein C1-C4Alkylene radical, C2-C4Alkenylene or C2-C4Alkynylene is unsubstituted or substituted by CN on at least one hydrogen atom, and/or by at least one-CH2-is substituted by-O-or-S-, and-O-is not directly linked to-O-or-S-and-S-is not directly linked to-S-; and
u is 0, 1 or 2.
The liquid crystal composition of the present invention comprises a first component, wherein the first component may comprise one or more liquid crystal compounds represented by the above formula (I). For example, the liquid crystal compound that can be used for the first component includes: 4OSy1, 4OSy2, 4OSy3, 4OSy4, 2OSy4, 2OSy3, 2OSy2, 4OSy2V, V2OSy2V, ByO4, 4ByO4, 3ByO4, 2ByO2, 2ByO4, 2OGByO4, 2OGByO2, V1OGByO2, 2PGByO2, 2PGByO4, 3CGByO2, or 3CGByO 4.
As described above, in the liquid crystal compound having the structure of formula (I), the chemical structures thereof all include the specific benzene ring structure (i.e., 4 carbon atoms on the benzene ring are sequentially bonded to an oxygen atom, a fluorine atom and an oxygen atom) as described above. Further, liquid crystal compounds having the structures represented by the formulae (I-A), (I-B-1), (I-B-2) and (I-B-3) can have good UV stability. Since the first component comprises at least one liquid crystal compound represented by the above formula (I), the liquid crystal composition of the present invention can have both high vertical dielectric constant and good UV stability.
The liquid crystal composition of the present invention further comprises a second component, wherein the second component may comprise one or more compounds having the formula (II) as described above. For example, compounds that may be used in the second component include: 3CCV, 3CCV1, 3PTPO1, 3CPPF, 3CPGF, V2PTP2V, 3PGB2, 2PGB2, 3CPTP2, 5CCGF, 3CCP1, VCCP1, 5 CCPCF3、4CCPOCF3、3CCPOCF33CPP2, 3 CCPP GF, 3CPPC3, 3CPTPO2, 2CPYO2, 3CCYO1, 3CCPF, 3PYO2, 2CPYO2, 3CYO4, 3CCYO2, 2CC1OYO2 or 3CC 5.
The liquid crystal compound represented by the formula (II) includes a liquid crystal compound (e.g., 3CCV1, 3CC5) which can be used as a viscosity depressant, a liquid crystal compound (e.g., 3PTPO1, 3PGB2) which can provide a high Δ n, and a negative liquid crystal compound (e.g., 3PYO2, 2CPYO2, 3CYO4), so that the viscosity, Δ n and Δ of the liquid crystal composition can be adjusted by adjusting the content of the liquid crystal compound represented by the formula (II).
The liquid crystal composition of the present invention may optionally further comprise a third component, wherein the third component may comprise one or more compounds represented by formula (III):
Figure BDA0001417912590000091
wherein X4 is F, Cl, -CH3、-CF3、-OCH＝CF2or-OCF3；
R5 is H, C1-C10Alkyl or C2-C10Alkenyl radical, and wherein C1-C10Alkyl or C2-C10Alkenyl is unsubstituted or at least one-CH2-substituted by-O-, -S-, -CO-, -O-CO-, -CO-O-or-O-CO-O-and wherein-O-, -S-, -CO-, -O-CO-, -CO-O-and-O-CO-O-substituents are not directly attached to each other, and/or at least one hydrogen atom is replaced by a halogen atom, CN or CF3Substitution;
a4, A5, A6 and A7 are each independently 1, 4-phenylene, 1, 4-cyclohexylene, 2, 5-tetrahydropyranyl, dioxa-bicyclo [2.2.2 ] bicyclo]Octane-functional, divalent trioxa-bicyclo [2.2.2]Octane functional group or divalent 2, 5-indane functional group, and wherein the 1, 4-phenylene, 1, 4-cyclohexylene or divalent 2, 5-indane functional group is unsubstituted or at least one hydrogen atom is substituted by a halogen atom or CN, and/or at least one-CH2-is substituted by-O-, -N-or-S-, and wherein the-O-, -N-and-S-substituted atoms are not directly attached to each other;
z3, Z4 and Z5 are each independently a single bond, C1-C4Alkylene radical, C2-C4Alkenylene radical, C2-C4Alkynylene, -CO-O-, -O-CO-, and wherein C1-C4Alkylene radical, C2-C4Alkenylene or C2-C4Alkynylene is unsubstituted or at least one hydrogen atom is substituted by a halogen atom, and/or at least one-CH2-is substituted by-O-or-S-, and wherein-O-is not directly linked to-O-or-S-, S-is not directly linked to-S-, and
q, r, s and t are each independently an integer of 0, 1, 2 or 3, and q + r + s + t ≧ 3.
For example, compounds that may be used for the third component include: 3PGUQUF, 4PGUQUF, 5PGUQUF, 2RIGUQUF, 3doPUQUF, 2toUQUO2F、3doPUO2F、3doPUF、RIGUQUF、1RIGUO2F、2doPUO2F or 2 RIGUQUF.
In the compounds of formula (III) where one of the Z3, Z4 or Z5 moieties is a structural element-CF2O-or-OCF2At-time, the rotary viscosity can be reducedDegree (. gamma.1) and enhances dielectric anisotropy (. DELTA.). Since the rotational viscosity is proportional to the reaction time of the liquid crystal molecules, if the rotational viscosity can be reduced, the reaction speed of the liquid crystal molecules can be increased when a voltage is applied to the display. Thus, if the third component is used, it has the structural unit-CF2O-or-OCF2The compound (4) can further improve the dielectric anisotropy and the rotational viscosity of the liquid crystal composition.
In addition, in the compound represented by the above formula (III), when one of a4, a5, a6 or a7 is a structural unit RI, to or do (see the structural formula in table 1), the dielectric anisotropy can be further improved. In some embodiments, one of A4, A5, A6, or A7 of formula (III) is dioxa-bicyclo [2.2.2]Octane-functional, divalent trioxa-bicyclo [2.2.2]Octane functional group or divalent 2, 5-indan functional group, and wherein the divalent 2, 5-indan functional group is unsubstituted or at least one hydrogen atom is substituted by a F atom, and/or at least one-CH2-is substituted by-O-, and-O-is not directly linked to-O-.
Therefore, the dielectric anisotropy and viscosity of the liquid crystal composition can be adjusted to a desired range by appropriately selecting a4, a5, a6 or a7 of the compound represented by formula (III).
It will be understood by those skilled in the art that the liquid crystal composition may further comprise other liquid crystal compounds than the liquid crystal compounds represented by the above formula (I), formula (II) or formula (III), or other additives in appropriate amounts. In some embodiments, other additives may include, for example, chiral (chiral) dopants, UV stabilizers, antioxidants, radical scavengers, nanoparticles, and the like.
In some embodiments, the first component may be present in an amount ranging from about 0.1 to about 50 wt% and the second component may be present in an amount ranging from about 50 to about 99.9 wt%, based on the total weight of the liquid crystal composition taken as 100 wt%. In other embodiments, the first component may be present in an amount ranging from about 0.1 to 40 wt% and the second component may be present in an amount ranging from about 60 to 99.9 wt%, based on the total weight of the liquid crystal composition taken as 100 wt%. In other embodiments, the first component may be present in an amount ranging from about 0.1 to about 30 wt% and the second component may be present in an amount ranging from about 70 to about 99.9 wt%, based on the total weight of the liquid crystal composition taken as 100 wt%. In some embodiments, the liquid crystal composition may further include a third component in addition to the first component and the second component. In such embodiments, the first component may be present in an amount ranging from about 0.1 to 45 weight percent, the second component may be present in an amount ranging from about 10 to 90 weight percent, and the third component may be present in an amount ranging from about 1 to 45 weight percent. In other embodiments, the first component may be present in an amount ranging from about 0.1 to 40 wt%, the second component may be present in an amount ranging from about 20 to 90 wt%, and the third component may be present in an amount ranging from about 5 to 45 wt%. In other embodiments, the first component may be present in an amount ranging from about 0.1 to 35 wt%, the second component may be present in an amount ranging from about 30 to 90 wt%, and the third component may be present in an amount ranging from about 10 to 45 wt%.
The invention also provides a liquid crystal display device using the liquid crystal composition. FIG. 1 is a cross-sectional view of an LCD device 100 according to some embodiments of the present invention.
Referring to fig. 1, the liquid crystal display device 100 may include a first substrate 110, a second substrate 120 disposed opposite to the first substrate 110, and a liquid crystal layer 130 disposed between the first substrate 110 and the second substrate 120. The first substrate 110 and the second substrate 120 can be a conventional thin film transistor substrate and a color filter substrate, respectively. For simplicity, the materials, structures and methods of forming the first substrate 110 and the second substrate 120 are not described in detail herein.
The liquid crystal layer 130 of the liquid crystal display device 100 of the present invention uses the above liquid crystal composition, wherein the liquid crystal composition comprises a liquid crystal compound represented by formula (I). As described above, the liquid crystal compound represented by formula (I) has a high vertical dielectric constant and good UV stability. By using the liquid crystal compound represented by formula (I), the liquid crystal display device has better light transmittance, product yield and life cycle. In addition, by selecting the first component, the second component and/or the third component used in the liquid crystal composition and adjusting the weight ratio thereof, the dielectric anisotropy, the rotational viscosity and the elastic modulus of the liquid crystal composition can be adjusted to desired ranges. Therefore, the liquid crystal display device using the liquid crystal composition has the advantages of saving energy and improving the reaction speed, can also obtain better light penetration, is beneficial to switching between a bright state and a dark state, and solves the problem of residual image of the display. The liquid crystal composition of the present invention is suitable for all liquid crystal display devices. In some embodiments, the liquid crystal composition of the present invention has a high vertical dielectric constant, and thus can be suitably used in a Fringe Field Switching (FFS) type liquid crystal display device. In other embodiments, the liquid crystal composition of the present invention can be applied to other types of liquid crystal display devices.
In order to make the aforementioned and other objects, features, and advantages of the present invention comprehensible, several embodiments accompanied with figures are described below. Since the examples and comparative examples of the present invention use a plurality of liquid crystal compounds, for the sake of simplicity, the following combinations are provided as symbols, wherein each symbol corresponds to a structural unit as shown in table 1. The symbols of the liquid crystal compounds represented by formula (I) used in the examples and the corresponding chemical structures are shown in table 2 below.
TABLE 2
Figure BDA0001417912590000121
Figure BDA0001417912590000131
In this specification, a method for synthesizing a liquid crystal compound represented by the formula (I-B-1) is described with reference to 4ByO4 as an example. Further, a method for synthesizing a liquid crystal compound represented by the formula (I-B-2) or (I-B-3) will be described with 2OGByO4 as an example. Further, a method for synthesizing the liquid crystal compound represented by the formula (I-A) will be described with reference to 4OSy2 as an example.
Preparation example 1 preparation of 4ByO 4:
Figure BDA0001417912590000132
the synthesis scheme of liquid crystal compound 4ByO4 is shown above. The synthesis steps of compounds 2to 5 and liquid crystal compound 4ByO4 will be described in order below.
Compound 1(20g, 87mmol) and tetrahydrofuran (tetrahydrofuran, 120mL) were dissolved in a 500mL reaction flask with stirring. While in an ice bath, hydrogen peroxide (30-35%, 120mL) was slowly added to the reaction flask and reacted at room temperature for 2 hours. After completion of the reaction, extraction was performed with ethyl acetate and water, and the organic layer was collected. The solvent of the collected organic layer was removed using a rotary concentrator to obtain compound 2 (pale yellow solid).
Compound 2(8g, 40mmol), acetonitrile (120 mL), triethylamine (22 mL), and magnesium chloride (magnesium chloride, 6.4g, 67mmol) were dissolved in a 250mL reaction flask with stirring, and paraformaldehyde (paraformaldehyde, 7.2g, 240mmol) was added and heated under reflux for 8 hours. After completion of the reaction, dilute hydrochloric acid (1N, 300mL) was added, extraction was performed with ethyl acetate and water, and the organic layer was collected. The solvent of the collected organic layer was removed using a rotary concentrator, and recrystallization was performed using Hexane (Hexane) to obtain compound 3 (white solid).
Triphenylphosphine (triphenylphoshine, 40.1g, 153mmol) and dichloromethane (dichromethane, 150mL) were placed in a 500mL reaction flask and dissolved with stirring. A mixture of carbon tetrabromide (carbon tetrachloride, 38.1g, 115mmol) and methylene chloride (dichromethane, 110mL) was slowly charged into the reaction flask while cooling on ice. After 10 min triethylamine (triethylamine, 32mL) was added and a mixture of compound 3(8.8g, 38.3mmol) and dichloromethane (dichromethane, 40mL) was added to the reaction flask. After the reaction was carried out for 30 minutes in an ice bath, the reaction was carried out at room temperature for 1 hour. After completion of the reaction, extraction was performed using dichloromethane and water, and the organic layer was collected. The solvent of the collected organic layer was removed using a rotary concentrator, and column chromatography was performed to obtain compound 4 (dark red liquid).
Compound 4(5g, 13mmol), tetrahydrofuran (75mL), potassium phosphate (5.5 g, 26mmol) and cuprous iodide (copper (I) iodate, 0.123g, 0.65mmol) were dissolved in a 250mL reaction flask with stirring. The reaction was heated under reflux for 7 hours under nitrogen. After completion of the reaction, dilute hydrochloric acid (1N, 50mL) was added, extraction was performed with ethyl acetate and water, and the organic layer was collected. The solvent of the collected organic layer was removed using a rotary concentrator, and column chromatography was performed to obtain compound 5 (brown solid).
Compound 5(2.4g, 7.9mmol) and anhydrous tetrahydrofuran (40 mL) were dissolved in a 100mL reaction flask with stirring. N-butyllithium (n-butylllithium, 2.5M, 6.4mL, 16mmol) was slowly charged into a reaction flask at-78 ℃ and reacted for 1 hour. Subsequently, 1-iodobutane (1-iodobutane, 3.68g, 20mmol) was charged into a reaction flask at-78 ℃ and reacted for 1 hour under ice bath. After completion of the reaction, dilute hydrochloric acid (1N, 20mL) was added, extraction was performed with ethyl acetate and water, and the organic layer was collected. The solvent of the collected organic layer was removed by using a rotary concentrator, and column chromatography was performed to obtain liquid crystal compound 4ByO4 (colorless liquid).
The liquid crystal compound 4ByO4 was analyzed by nmr spectroscopy, and the obtained spectral information was as follows:1H NMR(CDCl3,400MHz):0.96-1.03(m,6H),1.39-1.48(m,2H),1.51-1.57(m,2H),1.70-1.78(m,2H),1.80-1.87(m,2H),2.77(t,J＝7.2Hz,2H),4.06(t,J＝6.4Hz,2H),6.32(d,J＝2.8Hz,1H),6.80(dd,J1＝7Hz,J2＝2Hz,1H)。
according to the above-described scheme for the synthesis of 4ByO4, the functional group R1 of the final product can be varied by using different compounds 1 as starting reactants in the initial synthesis step. Furthermore, the use of different bromoalkyl compounds as reactants in the final synthesis step for reaction with compound 5 can alter the functional group R2 of the final product. Therefore, other liquid crystal compounds represented by the formula (I-B-1) can be prepared according to the above synthetic scheme.
According to the synthetic procedure of 4ByO4, liquid crystal compound ByO4 (colorless liquid) was synthesized. The liquid crystal compound ByO4 was analyzed by nmr spectroscopy, and the resulting spectral information was as follows:1H NMR(CDCl3,400MHz):1.02(t,J＝7.2Hz,3H),1.50-1.58(m,2H),1.81-1.89(m,2H),4.08(t,J＝6.4Hz,2H),6.74(t,J＝2.4Hz,1H),6.91(dd,J1＝7Hz,J2＝2Hz,1H),7.64(d,J＝2.4Hz,1H)。
according to the synthetic scheme of 4ByO4, liquid crystal compound 2ByO4 (colorless liquid) was synthesized. Liquid crystal compound 2ByO4 was analyzed by nmr spectroscopy, and the obtained spectral information was as follows:1H NMR(CDCl3,400MHz):1.0(t,J＝7.6Hz,3H),1.33(t,J＝7.6Hz,3H),1.50-1.57(m,2H),1.80-1.87(m,2H),2.81(q,J＝7.6Hz,2H),4.06(t,J＝6.4Hz,2H),6.32(d,J＝2.8Hz,1H),6.80(dd,J1＝7Hz,J2＝2Hz,1H)。
according to the synthetic scheme of 4ByO4, liquid crystal compound 2ByO2 (colorless liquid) was synthesized. Liquid crystal compound 2ByO2 was analyzed by nmr spectroscopy, and the obtained spectral information was as follows:1H NMR(CDCl3,400MHz):1.36(t,J＝7.6Hz,3H),1.48(t,J＝7.6Hz,3H),2.81(q,J＝7.6Hz,2H),4.15(q,J＝7.2Hz,2H),6.33(d,J＝3.2Hz,1H),6.80(dd,J1＝6.8Hz,J2＝2Hz,1H)。
preparation example 2OGByO4 preparation:
Figure BDA0001417912590000151
the synthesis scheme of the liquid crystal compound 2OGByO4 is shown above. The synthetic procedure for compound 5 is as described above and is not repeated here. The procedure for synthesizing the liquid crystal compound 2OGByO4 will be explained below.
Compound 5(1g, 3.28mmol), tetrahydrofuran (65mL), water (13mL), and potassium carbonate (2.0 g, 14.7mmol) were dissolved in a 250mL reaction flask with stirring, and deoxygenated with nitrogen for 30 minutes. Thereafter, compound 6(1.2g, 6.5mmol) was added, tetrakis (triphenylphosphine) palladium (0, 0.19g, 0.164mmol) was added, and the reaction was heated under reflux for 5 hours. After completion of the reaction, extraction was performed with ethyl acetate and water, and the organic layer was collected. The solvent of the collected organic layer was removed using a rotary concentrator and further subjected to column chromatography to obtain liquid crystal compound 2OGByO4 (white solid).
The liquid crystal compound 2OGByO4 was analyzed by nmr spectroscopy, and the obtained spectral information was as follows:1H NMR(CDCl3,400MHz):1.19(t,J＝7.6Hz,3H),1.66(t,J＝6.8Hz,3H),1.72(q,J＝7.6Hz,2H),2.03(m,2H),4.26(t,J＝6.8Hz,2H),4.32(q,J＝6.8Hz,2H),6.95-7.01(m,2H),7.10(dd,J1＝6.8Hz,J2＝2.4Hz,1H),7.24(d,J＝2.8Hz,1H),7.44-7.50(m,1H)。
according to the above-described scheme for the synthesis of 4ByO4, the functional group R1 of the final product can be varied by using different compounds 1 as starting reactants in the initial synthesis step. Furthermore, according to the above synthetic scheme of 2OGByO4, the functional group R2 of the final product can be changed by using a different compound 6 as a reactant to react with compound 5 in the final synthetic step. Therefore, other liquid crystal compounds represented by the formula (I-B-2) or the formula (I-B-3) can be prepared according to the above-mentioned synthetic procedures.
According to the synthetic scheme of 2OGByO4, a liquid crystal compound 2OGByO2 (white solid) was synthesized. The liquid crystal compound 2OGByO2 was analyzed by nmr spectroscopy, and the obtained spectral information was as follows:1H NMR(CDCl3,400MHz):1.43-1.48(m,6H),4.12(q,J＝3.2Hz,4H),6.75-6.81(m,2H),6.88(d,J＝7.2Hz,1H),7.03(d,J＝2.4Hz,1H),7.25-7.30(m,1H)。
according to the synthetic scheme of 2OGByO4, a liquid crystal compound V1OGByO2 (white solid) was synthesized. The liquid crystal compound V1OGByO2 was analyzed by nmr spectroscopy, and the obtained spectral information was as follows:1H NMR(CDCl3,400MHz):1.47(t,J＝6.8Hz,3H),4.12(q,J＝7.2Hz,2H),4.61-4.63(m,2H),5.27-5.30(m,1H),5.41-5.46(m,1H),5.99-6.09(m,1H),6.76-6.83(m,2H),6.88(dd,J1＝7.2Hz,J2＝2Hz,1H),7.20(d,J＝2.8Hz,1H),7.25-7.31(m,1H)。
according to the synthetic scheme of 2OGByO4, a liquid crystal compound 2PGByO2 (white solid) was synthesized. The liquid crystal compound 2PGByO2 was analyzed by nmr spectroscopy, and the obtained spectral information was as follows:1H NMR(CDCl3,400MHz):1.27(t,J＝7.6Hz,3H),1.47(t,J＝6.8Hz,3H),2.69(q,J＝7.6Hz,2H),4.13(q,J＝6.8Hz,2H),6.88(dd,J1＝6.8Hz,J2＝1.6Hz,1H),7.15(t,J＝3.2Hz,1H),7.28(d,J＝8Hz,2H),7.38(dd,J1＝12.4Hz,J2＝1.6Hz,1H),7.47(dd,J1＝8.4Hz,J2＝1.6Hz,1H),7.53(d,J＝8.4Hz,2H),8.05(t,J＝8Hz,1H)。
according to the synthetic scheme of 2OGByO4, a liquid crystal compound 2PGByO4 (white solid) was synthesized. The liquid crystal compound 2PGByO4 was analyzed by nmr spectroscopy, and the obtained spectral information was as follows:1H NMR(CDCl3,400MHz):0.98(t,J＝7.6Hz,3H),1.25-1.29(m,3H),1.48-1.53(m,2H),1.79-1.86(m,2H),2.69(q,J＝7.6Hz,2H),4.06(t,J＝6.8Hz,2H),6.88(d,J＝6.8Hz,1H),7.28(d,J＝7.6Hz,2H),7.38(d,J＝12.8Hz,1H),7.47(d,J＝8Hz,1H),7.53(d,J＝7.6Hz,2H),8.04(t,J＝8Hz,1H)。
according to the synthetic scheme of 2OGByO4, a liquid crystal compound 3CGByO2 (white solid) was synthesized. The liquid crystal compound 3CGByO2 was analyzed by nmr spectroscopy, and the obtained spectral information was as follows:1H NMR(CDCl3,400MHz):0.89(t,J＝7.2Hz,3H),0.99-1.10(m,2H),1.19-1.23(m,3H),1.28-1.36(m,3H),1.41-1.48(m,4H),1.84-1.92(m,4H),2.45-2.52(m,1H),4.12(q,J＝7.2Hz,2H),6.85(dd,J1＝7.2Hz,J2＝1.6Hz,1H),6.99(dd,J1＝12.4Hz,J2＝1.6Hz,1H),7.05-7.09(m,2H),7.89(t,J＝8Hz,1H)。
according to the synthetic scheme of 2OGByO4, a liquid crystal compound 3CGByO4 (white solid) was synthesized. The liquid crystal compound 3CGByO4 was analyzed by nmr spectroscopy, and the obtained spectral information was as follows:1H NMR(CDCl3,400MHz):0.89(t,J＝7.2Hz,3H),0.98(t,J＝7.6Hz,3H),1.10-1.54(m,11H),1.78-1.91(m,6H),2.45-2.51(m,1H),4.04(t,J＝6.8Hz,2H),6.85(dd,J1＝6.8Hz,J2＝1.6Hz,1H),6.99(d,J＝12.8Hz,1H),7.05-7.09(m,2H),7.89(t,J＝8Hz,1H)。
preparation example 3 preparation of 4OSy 2:
Figure BDA0001417912590000171
the synthetic scheme of liquid crystal compound 4OSy2 is shown above. The synthetic procedures for compounds 1-3 are as described above and are not repeated here. The procedure for synthesizing liquid crystal compound 4OSy2 will be described below.
Compound 3(3g, 13mmol), tetrahydrofuran (10mL) and methanol (10mL) were dissolved in a 100mL reaction flask with stirring. Sodium borohydride (1.5 g, 39.5mmol) was slowly added to the reaction flask while cooling on ice. The reaction was carried out at room temperature for 8 hours. After completion of the reaction, extraction was performed with ethyl acetate and water, and the organic layer was collected. The solvent of the collected organic layer was removed using a rotary concentrator, and column chromatography was performed to obtain compound 7 (brown solid).
Compound 7(3g, 12.9mmol), toluene (tolumen, 180mL), propionaldehyde (propionaldehyde, 1.13g, 19.5mmol) and p-toluenesulfonic acid monohydrate (p-tolenesulfonic acid monohydrate, 0.42g, 2.2mmol) were dissolved in a 250mL reaction flask with stirring and reacted for 8 hours. After completion of the reaction, extraction was performed with ethyl acetate and water, and an organic layer was collected. The solvent of the collected organic layer was removed using a rotary concentrator, and column chromatography was performed to obtain liquid crystal compound 4OSy2 (colorless liquid).
The liquid crystal compound 4OSy2 was analyzed by nmr spectroscopy, and the obtained spectral information was as follows:1H NMR(CDCl3,400MHz):0.99(t,J＝7.6Hz,3H),1.09(t,J＝7.6Hz,3H),1.46-1.55(m,2H),1.75-1.82(m,2H),1.86-1.99(m,2H),3.97(t,J＝6.4Hz,2H),4.79(d,J＝14.4Hz,1H),4.91-4.98(m,2H),6.35(dd,J1＝8Hz,J2＝2.4Hz,1H)。
according to the above-described scheme for the synthesis of 4OSy2, the functional group R1 of the final product can be varied by using different compounds 1 as starting reactants in the initial synthesis step. Furthermore, according to the above-mentioned synthetic scheme of 4OSy2, the functional group R2 of the final product can be changed by using different aldehyde compounds as reactants for the reaction with the compound 7 in the final synthetic step. Therefore, other liquid crystal compounds represented by the formula (I-A) can be prepared according to the above-mentioned synthetic procedures.
According to the synthetic scheme of 4OSy2, liquid crystal compound 2OSy2 (white solid) was synthesized. Liquid crystal compound 2OSy2 was analyzed by nmr spectroscopy, and the obtained spectral information was as follows:1H NMR(CDCl3,400MHz):1.09(t,J＝7.6Hz,3H),1.43(t,J＝7.2Hz,3H),1.86-1.99(m,2H),4.04(q,J＝6.8Hz,2H),4.79(d,J＝15.2Hz,1H),4.91-4.98(m,2H),6.35(dd,J1＝8Hz,J2＝2Hz,1H)。
according to the synthetic scheme of 4OSy2, liquid crystal compound 2OSy4 (white solid) was synthesized. Liquid crystal compound 2OSy4 was analyzed by nmr spectroscopy, and the obtained spectral information was as follows:1H NMR(CDCl3,400MHz):0.96(t,J＝7.2Hz,3H),1.37-1.46(m,5H),1.49-1.57(m,2H),1.84-1.95(m,2H),4.04(q,J＝7.2Hz,2H),4.79(d,J＝14.8Hz,1H),4.93(d,J＝14.8Hz,1H),5.01(t,J＝5.2Hz,1H),6.35(dd,J1＝8Hz,J2＝2Hz,1H)。
according to the synthetic scheme of 4OSy2, liquid crystal compound 4OSy4 (colorless liquid) was synthesized. The liquid crystal compound 4OSy4 was analyzed by nmr spectroscopy, and the obtained spectral information was as follows:1H NMR(CDCl3,400MHz):0.94-1.01(m,6H),1.37-1.57(m,6H),1.74-1.82(m,2H),1.83-1.96(m,2H),3.97(t,J＝6.4Hz,2H),4.79(d,J＝14.4Hz,1H),4.93(d,J＝14.4Hz,1H),5.01(t,5.2Hz,1H),6.35(dd,J1＝8Hz,J2＝2.4Hz,1H)。
according to the synthetic scheme of 4OSy2, liquid crystal compound 4OSy2V (colorless liquid) was synthesized. The liquid crystal compound 4OSy2V was analyzed by nmr spectroscopy, and the obtained spectral information was as follows:1H NMR(CDCl3,400MHz):0.99(t,J＝7.6Hz,3H),1.45-1.55(m,2H),1.74-1.82(m,2H),1.92-2.07(m,2H),2.29-2.35(m,2H),3.97(t,J＝6.4Hz,2H),4.79(d,J＝14.4Hz,1H),4.93(d,J＝14.4Hz,1H),5.01-5.05(m,2H),5.08-5.13(m,1H),5.83-5.93(m,1H),6.35(dd,J1＝8Hz,J2＝2.4Hz,1H)。
according to the synthetic scheme of 4OSy2, a liquid crystal compound V2OSy2V (colorless liquid) was synthesized. The liquid crystal compound V2OSy2V was analyzed by nmr spectroscopy, and the obtained spectral information was as follows:1H NMR(CDCl3,400MHz):1.98-2.01(m,2H),2.30-2.33(m,2H),2.53-2.58(m,2H),4.02(t,J＝6.8Hz,2H),4.79(d,J＝14.4Hz,1H),4.92(d,J＝14Hz,1H),5.02-5.05(m,2H),5.08-5.22(m,3H),5.83-5.95(m,2H),6.36(dd,J1＝8Hz,J2＝2Hz,1H)。
measurement of Properties of liquid Crystal Compound
The properties of the liquid crystal compound represented by the formula (I) were measured by the following methods, respectively. The liquid crystal compounds represented by the formula (I) shown in Table 1 were prepared by the above-mentioned synthesis procedures. Commercially available compounds 2CCGF, 3CCGF and 5CCGF were directly mixed at a weight ratio of 1:1:1 to prepare a mother liquor. The liquid crystal compounds listed in Table 1 were mixed in the mother liquor in the weight ratios listed in tables 3, 4 and 5, respectively. The properties of the liquid crystal compounds were measured by the following experimental procedures and the results are shown in tables 3, 4 and 5, respectively.
[ vertical dielectric constant: (⊥) And dielectric anisotropy (. DELTA.)]
The liquid crystal compound was charged into a cell having an average cell gap of 9 μm, and a voltage of 20V to 50V was applied to the cell at a temperature of 25 ℃. An average dielectric constant measured in a direction parallel to the long axis of the liquid crystal molecules of||(ii) a An average dielectric constant measured perpendicular to the long axis of the liquid crystal molecules of⊥. Dielectric anisotropy (. DELTA.) of||And⊥is (i.e., Δ ═ a)||-⊥)。
[ refractive index anisotropy (. DELTA.n) ]
The surface of the main prism was wiped in one direction, a small amount of a liquid crystal compound was dropped on the main prism, and measurement was performed at 25 ℃ using an Abbe refractometer having an eyepiece equipped with a polarizing plate using a filter having a wavelength of 598 nm. When the polarization direction was parallel to the rubbing direction, the refractive index was measured as n||(ii) a When the polarization direction was perpendicular to the rubbing direction, the refractive index was measured as n⊥. The refractive index anisotropy (Delta n) is formed by n||And n⊥Is obtained by (i.e., Δ n ═ n)||-n⊥)。
[ rotational viscosity (. gamma.1) ]
The rotational viscosity (. gamma.1) was obtained by charging a liquid crystal compound into a cell having an average cell gap of 9 μm, applying a voltage of 20V to the cell at a temperature of 25 ℃ and converting the voltage into a dielectric anisotropy (. DELTA.) factor by an instrument.
[ UV stability ]
The liquid crystal was charged into a cell having an average gap of 9 μm, and the dielectric anisotropy was measured to obtain an initial value Δ of the dielectric anisotropy. After the cell was irradiated with UV light for 90 minutes, the dielectric anisotropy was measured again to obtain the final value Δ 'of the dielectric anisotropy, and the UV stability data was obtained by dividing Δ' by Δ and multiplying by 100%.
TABLE 3
Figure BDA0001417912590000201
As shown in Table 3, the liquid crystal compounds represented by the formula (I-A) all had high vertical dielectric constants: (⊥>14). Furthermore, the liquid crystal compound represented by the formula (I-A) showed a change in dielectric anisotropy (. DELTA.) of. + -. 2% after 90 minutes of UV light irradiation, and no change in dielectric anisotropy (. DELTA.) was realized. Thus, it is understood that the liquid crystal compound having the structural unit OSy can combine a high vertical dielectric constant with excellent UV stability.
TABLE 4
Code number ByO4 2ByO2 2ByO4 4ByO4
Weight ratio (wt%) 10.00 10.00 10.00 10.00
Δε 3.55 0.99 -0.66 -2.17
ε⊥ 16.94 15.44 16.47 15.61
γ1 -198.60 -964.50 -147.30 -75.40
Δn 0.0206 0.0364 0.0415 0.0360
UV stability (%) 98.80 99.80 100.00 98.60
As shown in Table 4, the liquid crystal compounds represented by the formula (I-B-1) all had high vertical dielectric constants: (⊥>15). Furthermore, the liquid crystal compound represented by the formula (I-B-1) showed a change in dielectric anisotropy (. DELTA.) of. + -. 2% after 90 minutes of UV light irradiation, and no change in dielectric anisotropy (. DELTA.) was realized. From this fact, it is understood that the liquid crystal compound having the structural unit ByO can combine a high vertical dielectric constant with excellent UV stability.
TABLE 5
Figure BDA0001417912590000202
Figure BDA0001417912590000211
The liquid crystal compounds represented by the formula (I-B-2) or (I-B-3) each have a structure in which the structural unit G is directly bonded to the left of the structural unit ByO. As shown in Table 4, the liquid crystal compounds represented by the formula (I-B-2) or the formula (I-B-3) each had a high vertical dielectric constant (I-B-2)⊥>7.5). Furthermore, the liquid crystal compound represented by the formula (I-B-2) or the formula (I-B-3) showed a change in dielectric anisotropy (. DELTA.) of. + -. 4% after 90 minutes of UV light irradiation, and no change in dielectric anisotropy (. DELTA.) was observed. From these results, it was found that the liquid crystal compounds represented by the formula (I-B-2) or (I-B-3) have excellent UV stability while maintaining a moderately high vertical dielectric constant.
TABLE 6
Figure BDA0001417912590000212
In order to confirm the merits of the liquid crystal compound represented by formula (I-B-1), the results of the control experiment are shown in Table 6. Referring to Table 1, the carbon atom to which the structural unit ByO is bonded to the functional group X has a double bond (i.e., is in an unsaturated state); the carbon atom to which structural unit tYO is bonded to functional group X has 4 single bonds (i.e., in a saturated state). Referring to Table 4, the liquid crystal compounds listed in Table 4 are all liquid crystal compounds represented by formula (I-B-1), and their viscosities (. gamma.1) are all negative. In contrast, the viscosity (γ 1) of the liquid crystal compound 4tYO4 of table 6 was greater than 17. It can be demonstrated that, in the liquid crystal compound represented by the formula (I-B-1) in the present case, the carbon atom bonded to the functional group R2 includes a double bond, and such a structure contributes to the reduction of the viscosity of the liquid crystal compound.
Furthermore, the results of the control experiment are also shown in Table 6 in order to confirm the advantages of the liquid crystal compounds represented by the formula (I-B-2) or the formula (I-B-3). Referring to Table 1, structural element G isA fluorine substituent is arranged at a specific position of a benzene ring; the structural unit P does not have any fluorine substituent on the benzene ring. Referring to Table 5, the liquid crystal compounds listed in Table 5 are all the liquid crystal compounds represented by formula (I-B-2) or formula (I-B-3) (i.e., the liquid crystal compounds have the structure in which the structural unit G is directly bonded to the left of the structural unit ByO), and the dielectric anisotropy (Δ) of the liquid crystal compounds changes by + -4% after being irradiated with UV light for 90 minutes, even though no change in the dielectric anisotropy (Δ) can be achieved. In contrast, when the weight ratio of the liquid crystal compound 2PByO4 in table 6 was 7.5%, the dielectric anisotropy (Δ) was changed to ± 4% after the UV light irradiation for 43 seconds; after 90 minutes of UV light irradiation, the liquid crystal compound had precipitated and the amount of change in dielectric anisotropy (Δ) could not be measured at all. On the other hand, as is clear from table 6, the weight ratio of the liquid crystal compound 2PByO4 must be lower than a specific range (for example, 2.5% or less) to maintain the required UV stability. As a result, the content of the compound used in the liquid crystal composition is limited, which is not favorable for imparting a high vertical dielectric constant (⊥)。
Liquid crystal composition
The liquid crystal composition comprises a first component, a second component and/or a third component, wherein the first component, the second component and the third component respectively comprise one or more liquid crystal compounds represented by a formula (I), a formula (II) and a formula (III).
The synthesis of the compounds of formula (I) is described above and will not be described in detail. As the compound represented by the formula (II), a commercially available liquid crystal molecule (for example, compound 3CCV is available from Kyoto Kingson Sun). The compound represented by the formula (III) is prepared according to the synthetic procedure described in taiwan patent No. TW I462993B.
The liquid crystal composition of the present invention was prepared by directly mixing all the liquid crystal compounds of the first, second and third components described above in the amounts shown in tables 7, 8 and 9 below. The methods for measuring the properties of the liquid crystal composition examples and comparative examples of the present invention are as described above. The results of measuring the properties are also shown in tables 7, 8 and 9. It is noted that, in tables 7, 8 and 9, the content unit of the liquid crystal compound is wt% (calculated as 100 wt% of the total weight of the liquid crystal composition).
TABLE 7
Figure BDA0001417912590000231
Figure BDA0001417912590000241
Figure BDA0001417912590000251
Figure BDA0001417912590000261
Figure BDA0001417912590000271
Please refer to Table 7 for comparative example C-1 and examples E-1-1, E-1-2 and E-1-3, wherein examples E-1-1, E-1-2 and E-1-3 all include the first component (4OSy2 or 4ByO4), and comparative example C-1 does not include the first component. The results show that the liquid crystal compound represented by the formula (I) can impart a high vertical dielectric constant to the liquid crystal composition: (⊥). In other words, the liquid crystal composition of the present invention has the advantage of higher light transmittance due to the inclusion of the liquid crystal compound represented by the above formula (I).
Refer to examples E-1-1 and E-1-3 of Table 7, wherein example E-1-1 includes the third component and example E-1-3 does not include the third component. The results show that if the third component comprising the structural unit RI and the structural unit P is added, the vertical dielectric constant of the liquid crystal composition can be further improved (⊥) And the rotational viscosity (γ 1) of the liquid crystal composition can be further reduced. In other words, the vertical dielectric constant and the rotational viscosity of the liquid crystal composition can be adjusted to a desired range by changing the content of the third component and the constitutional unit of the third component as needed.
Referring to comparative example C-2 and examples E-2-1 to E-2-9 of Table 8, examples E-2-1 to E-2-9 all included the liquid crystal compound represented by formula (I-B-2) or formula (I-B-3), and comparative example C-2 did not include the liquid crystal compound represented by formula (I-B-2) or formula (I-B-3). The results showed that the liquid crystal compound represented by the formula (I-B-2) or the formula (I-B-3) can provide a liquid crystal composition having a suitable vertical dielectric constant (for example,⊥greater than about 4) and rotational viscosity (e.g., γ 1 less than about 80). In other words, if the liquid crystal compound represented by the formula (I-B-2) or (I-B-3) is used as the first component, the vertical dielectric constant and the rotational viscosity of the liquid crystal composition can be adjusted to a desired range by changing the structural unit and the content thereof as required.
Referring to comparative example C-3 and examples E-3-1 to E-3-10 of Table 9, examples E-3-1 to E-3-10 all included the liquid crystal compound represented by formula (I), and comparative example C-3 did not include the liquid crystal compound represented by formula (I). The results show that the liquid crystal compound represented by formula (I) can impart a liquid crystal composition with a suitable vertical dielectric constant (for example,⊥greater than about 5) and rotational viscosity (e.g., γ 1 is less than about 90). In other words, the vertical dielectric constant and the rotational viscosity of the liquid crystal composition can be adjusted to a desired range by changing the structural unit and the content of the liquid crystal compound represented by formula (I).
In summary, the liquid crystal compounds of the present invention can have high vertical dielectric constant: (⊥Greater than 10) and excellent UV stability (dielectric anisotropy change by UV light irradiation for 90 minutes is ± 5%). The liquid crystal composition of the present invention can maintain a moderately high vertical dielectric constant due to the inclusion of the liquid crystal compound of the present invention⊥Greater than 5) while reducing the rotational viscosity (γ 1 less than 90). Further, by selecting the compounds used for the first component, the second component and the third component and adjusting the content ratio of the first component, the second component and the third component, Δ,⊥The values of γ 1 and/or K11 are adjusted to the desired range. In addition, the liquid crystal display device using the liquid crystal composition can have better light transmittance, energy conservation and reactionThe speed is high.
Although the present invention has been described with reference to a few preferred embodiments, it should be understood that various changes and modifications can be made therein by those skilled in the art without departing from the spirit and scope of the invention as defined by the appended claims.
Description of the symbols
100-liquid crystal display device
110 to the first substrate
120 to the second substrate
130-liquid crystal layer

Claims (10)

1. A liquid crystal compound having a structure represented by formula (I):
Figure FDA0002584021420000011
wherein n1, n2, X1, X2, X3, R1 and R2 are defined as follows:
(1) n1 ═ 0, n2 ═ 0, and X1 are
Figure FDA0002584021420000012
X2 is-O-and X3 is-CH2In this case R1, R2 are each, independently of one another, H, C1-C15Alkyl radical, C2-C15Alkenyl or C2-C15Alkynyl, and wherein C1-C15Alkyl radical, C2-C15Alkenyl or C2-C15Alkynyl is unsubstituted or at least one-CH2-by-CF2O-, -CO-O-or-O-CO-and/or at least one hydrogen atom is replaced by a halogen atom; or
(2) n1 ═ 0, n2 ═ 0, and X1 are
Figure FDA0002584021420000013
X2 is ═ CH-, and X3 is a single bond, in which case R1, R2 are each, independently of one another, H, C1-C15Alkyl radical, C2-C15Alkenyl or C2-C15Alkynyl, and wherein C1-C15Alkyl radical, C2-C15Alkenyl or C2-C15Alkynyl is unsubstituted or at least one-CH2-by-CF2O-, -CO-O-or-O-CO-and/or at least one hydrogen atom is replaced by a halogen atom; or
(3) n1 ═ 1, n2 ═ 1 or 0, and X1 is
Figure FDA0002584021420000014
X2 is ═ CH-, and X3 is a single bond, when R1 and R2 are each independently of the other H, a halogen atom, C1-C15Alkyl radical, C2-C15Alkenyl or C2-C15Alkynyl, and wherein C1-C15Alkyl radical, C2-C15Alkenyl or C2-C15Alkynyl is unsubstituted or at least one-CH2-by-CF2O-, -CO-O-or-O-CO-and/or at least one hydrogen atom is replaced by a halogen atom, the cyclic group A is 1, 4-phenylene or 1, 4-cyclohexylene,
wherein the liquid crystal compound is not
Figure FDA0002584021420000015
2. The liquid crystal compound of claim 1, wherein in (1), at least one of R1, R2 is unsubstituted C1-C15Alkyl or unsubstituted C2-C15An alkenyl group.
3. A liquid crystal compound according to claim 1, wherein in (2), at least one of R1 and R2 is C1-C15Alkyl or C2-C15An alkenyl group.
4. A liquid crystal composition comprising a first component and a second component, wherein the first component comprises one or more liquid crystal compounds according to claim 1 and the second component comprises one or more compounds of formula (II):
Figure FDA0002584021420000021
wherein R3, R4 are each independently H, C1-C15Alkyl or C2-C15Alkenyl radical, and wherein C1-C15Alkyl or C2-C15Alkenyl is unsubstituted, and/or at least one-CH2-is substituted by-O-and-O-is not directly linked to-O-;
a1, A2, A3 are each independently 1, 4-phenylene, 1, 4-cyclohexylene, 2, 5-benzofuranylene or 2, 5-tetrahydropyranyl, wherein 1, 4-phenylene, 1, 4-cyclohexylene, 2, 5-benzofuranylene or 2, 5-tetrahydropyranyl is unsubstituted or at least one hydrogen atom is substituted by a F atom;
z1 and Z2 are each independently a single bond, C1-C4Alkylene radical, C2-C4Alkenylene radical, C2-C4Alkynylene, and wherein C1-C4Alkylene radical, C2-C4Alkenylene or C2-C4Alkynylene is unsubstituted or substituted by CN on at least one hydrogen atom, and/or by at least one-CH2-is substituted by-O-or-S-, and-O-is not directly linked to-O-or-S-and-S-is not directly linked to-S-; and
u is 0, 1 or 2.
5. A liquid crystal composition of claim 4 further comprising a third component, wherein the third component comprises one or more compounds of formula (III):
Figure FDA0002584021420000022
wherein X4 is F, Cl, -CF3、-OCH＝CF2or-OCF3；
R5 is H, C1-C10Alkyl or C2-C10Alkenyl radical, and wherein C1-C10Alkyl or C2-C10Alkenyl is unsubstituted or at least one-CH2-substituted by-O-, -S-, -CO-, -O-CO-, -CO-O-or-O-CO-O-and wherein-O-, -S-, -CO-, -O-CO-, -CO-O-and-O-CO-O-substituents are not directly attached to each other, and/or at least one hydrogen atom is replaced by a halogen atom, CN or CF3Substitution;
a4, A5, A6 and A7 are each independently 1, 4-phenylene, 1, 4-cyclohexylene, 2, 5-tetrahydropyranyl, dioxa-bicyclo [2.2.2 ] bicyclo]Octane-functional, divalent trioxa-bicyclo [2.2.2]Octane functional group or divalent 2, 5-indane functional group, and wherein the 1, 4-phenylene, 1, 4-cyclohexylene or divalent 2, 5-indane functional group is unsubstituted or at least one hydrogen atom is substituted by a halogen atom or CN, and/or at least one-CH2-is substituted by-O-, -N-or-S-, and wherein the-O-, -N-and-S-substituted atoms are not directly attached to each other;
z3, Z4 and Z5 are each independently a single bond, C1-C4Alkylene radical, C2-C4Alkenylene radical, C2-C4Alkynylene, -CO-O-, -O-CO-, and wherein C1-C4Alkylene radical, C2-C4Alkenylene or C2-C4Alkynylene is unsubstituted or at least one hydrogen atom is substituted by a halogen atom, and/or at least one-CH2-is substituted by-O-or-S-, and wherein-O-is not directly linked to-O-or-S-and-S-is not directly linked to-S-; and
q, r, s and t are each independently an integer of 0, 1, 2 or 3, and q + r + s + t ≧ 3.
6. A liquid crystal composition of claim 5 wherein the third component comprises a compound of formula (III) and at least one of A4, A5, A6, A7 of the compound of formula (III) is dioxa-bicyclo [2.2.2]Octane-functional, divalent trioxa-bicyclo [2.2.2]Octane functional group or divalent 2, 5-indan functional group, and wherein the divalent 2, 5-indan functional group is unsubstituted or at least one hydrogen atom is substituted by a F atom, and/or at least one-CH2-is substituted by-O-, and-O-is not directly linked to-O-.
7. A liquid crystal composition of claim 5, wherein the third component comprises a compound of formula (III) and at least one of A4, A5, A6, A7 of the compound of formula (III) is 1, 4-phenylene, and wherein 1, 4-phenylene is unsubstituted or at least one hydrogen atom is substituted with a F atom.
8. The liquid crystal composition of claim 4, wherein the first component is 0.1 to 50 wt% and the second component is 50 to 99.9 wt% based on 100 wt% of the total weight of the liquid crystal composition.
9. The liquid crystal composition of any one of claims 5 to 7, wherein the first component is 0.1 to 45 wt%, the second component is 10 to 90 wt%, and the third component is 1 to 45 wt% calculated as 100 wt% of the total weight of the liquid crystal composition.
10. A liquid crystal display device comprising:
a first substrate;
a second substrate disposed opposite to the first substrate;
a liquid crystal layer between the first substrate and the second substrate, wherein the liquid crystal layer comprises the liquid crystal compound according to claim 1.
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